


Life By A Thousand Choices

by LilacRainCoffee23



Category: Gilmore Girls
Genre: Canon Related, Coffee Shops, F/M, Falling In Love, New York City, Pre-AYITL, Relationship(s), Slow Burn
Language: English
Status: In-Progress
Published: 2020-08-30
Updated: 2020-09-30
Packaged: 2021-03-06 15:48:56
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 13,999
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26181412
Author URL: https://archiveofourown.org/users/LilacRainCoffee23/pseuds/LilacRainCoffee23
Summary: What happened in those years after Rory graduated from Yale and before she left us with those four, infamous words? Jess has moved back to Stars Hollow and Rory is visiting home for her twenty-sixth birthday. She quickly finds herself in a situation that could change the course of her life forever––but only if she has the courage to follow her gut. Is Rory ready to give in to the wonder and chaos of a life she hasn't thoroughly planned?Set four years after Rory’s senior year at Yale and six years before A Year In The Life.
Relationships: Luke Danes/Lorelai Gilmore, Rory Gilmore/Jess Mariano
Comments: 16
Kudos: 57





	1. Happy Birthday, Rory Gilmore

**Author's Note:**

> This is my first stab at writing a fic in uh *checks notes* thirteen years! After rewatching Gilmore Girls, I'm feeling super inspired. I appreciate any and all readers, as well as comments. I hope I'm doing this thing right.

Autumn was always the prettiest time of year in Stars Hollow. The leaves started to change colors, the humidity coming in from the ocean lifted, the tourists went away (back to New York or Chicago or wherever-the-hell they’d come from in the first place) and the string lights that Kirk had nearly hung himself trying to drape perfectly around the gazebo glowed just a little warmer. 

As Rory made her way through the town square, she tried to focus on the perfectly crisp and cool New England weather and not on the reason she was home: her twenty-sixth birthday. _Twenty-six._ What a stupid age. It felt like a layover between the mess of her early twenties and the promise of her early thirties. But not a cool layover or even a long layover. An inconvenient layover. Enough time for her to seemingly screw up her life, but not enough time to put it all back together again.

She was supposed to have won a Pulitzer, authored her own column in The Paris Review, and shaken Fran Lebowitz’s hand by now! Everything she thought she’d have accomplished by almost-thirty seemed more and more naive with each year that passed. But nevertheless, she couldn’t help but ask herself––what had she accomplished?

Well, she’d ordered Chinese food from a pancake place on her last day, ever, as a twenty-five year old. She had saved exactly thirty-three hundred dollars of her own money in her own bank account, despite paying insane Brooklyn rent. And she had a promising editorial internship with a food magazine. And this time it was _paid._

She yanked open the door to Al’s Pancake World, bringing in with her a gust of wind that sent a table of tourists chasing after their napkins and menus. 

“Sorry!” she said, picking up a rogue napkin off the floor and placing it back on the tourists’ table. “Hurricane season, am I right?”

They gave her a scorching look, confirming that they were indeed from out of town. New Yorkers. _Whoops_. 

“Rory!” A voice squeaked behind her, immediately yanking her attention away from the black-cardigan-clad tourists and their vicious, unforgiving look. She spun around on her heels. 

“Babette!”

“Aw, sweetie,” Babette croaked, placing her manicured hands on either side of Rory’s face. “It is so good to see you. It feels like it’s been _forever._ It’s your birthday, isn’t it? Aw, that’s so nice. Anyway, listen, I need you to do me a favor.” She dropped her hands and gazed up at Rory from beneath her wispy blond bangs, lowering her voice to a stage whisper. “Luke’s nephew––Jess. You know him? Ah, what am I saying! Of course you know Jess. You’re not still upset about that, are you, sweetie?” 

Rory loved Babette––to death. But she could see her order (two kung pao chickens, one shrimp lo mein, an order of egg rolls, two orders of crab rangoons, and a stack of pumpkin spice pancakes) sitting in a to-go bag on the counter, getting cold. Lorelai and Luke were waiting for her at home, their DVR filled with old episodes of Mad TV just waiting to be watched. The last thing Rory wanted to be doing right now was talking to Babette about an ex-boyfriend from ten years ago. 

“No, Babette, of course not. I haven’t thought about him in…”

“Oh, boy,” Babette cut her off, giving her hands a squeeze as her blue eyes widened. “Too late.” 

And just like that, she was gone, scurrying back towards the table she’d come from.

“Wait––”

“Rory.” 

Her stomach suddenly felt like it had been dunked into a vat of ice water. Her jaw locked and her legs froze. _No, Babette, of course not._

She willed herself to turn slowly towards the voice.

“Jess.”

There he was. Taller than she remembered. And bulkier, too. Like maybe he’d started lifting weights or doing that P90X thing everyone wouldn’t shut up about. _Yeah, he’s definitely started lifting weight_ , she thought. His shoulders seemed to have doubled in width. And _his hair._ His thick, jet black hair. It was longer, flopping over to the side and hanging near his eyes which were still dark and deep, almost bottomless. He had a mustache now, too. Thick, but trimmed perfectly around his lips. 

He was smiling, his arms held out open at his sides. He looked so _happy._

She grinned, “What are you doing here?” 

“I could ask the same thing about you.” All the stuff that had her frozen in her spot melted away and she lunged forward to give him a hug. His jean jacket smelled the way it always had––like firewood and aftershave. He squeezed her tight.

“It’s my birthday. My twenty-sixth birthday, to be exact. I’m home celebrating with mom and Luke,” she said, pulling away. 

His eyes traced her up and down, making her suddenly self-conscious of the baby blue t-shirt and out-dated jeans she’d thrown on to pick up the food. “You look great. And, of course, how could I forget? You’re a libra.”

“A _libra_? Is that the kind of stuff you bohemians talk about in Philly?”

He laughed and dropped his eyes, awkwardly placing his hands on his hips. “I actually moved back… here. To Stars Hollow.”

“Oh.” That was all she could say. Her stomach did the ice-water thing again. “But what about your publishing career? What about your writing? You haven’t given up, have you?” she blustered, trying to fill the dead air. 

“It’s all good, I promise,” he chuckled. “Don’t panic, I haven’t given up yet. I'm still the poor man's Stephen King. It’s just this whole internet thing is really putting a wrench in our plans for the year.”

She couldn’t help but laugh, shaking her head. “Yeah, this whole internet thing tends to do that. Not a great time to be a novelist or a journalist.” 

He nodded. “I just needed to step away for a while, to figure some things out. So, I’m renting a cottage from Taylor for the fall. Going to work on my next book.” She felt a swell of pride in her chest. Here they were––two grown adults with careers and novels and aspirations. She always knew Jess would be somebody. She hoped he felt the same way about her too.

“Whoa, Taylor the landlord.”

He laughed at that, a big laugh that showed off his crooked smile, making her blush. “Exactly.”

Rory cleared her throat, hoping it would stop the smile. It had been a few years since they’d seen each other, since they’d kissed. She’d always thought if she ever saw Jess again it would feel at best like nothing and at worst, well, _bad_. But here they were, laughing. 

“Well, I should settle my debts with Al before he sends the constable after me. You know, small town things.” 

He nodded, “Let’s get coffee sometime, ok?”

She backed up towards the counter, “Sure. You have my number, right?”

He stayed quiet for a moment, barely moving, just licking his lips.

"Yeah, actually, I do.”

She let the smile come back again. “Perfect. Text me.”

~*~

“Why didn’t you tell me Jess moved home?” She hissed under her breath at Lorelai as they stood around the kitchen table, unpacking the food. Luke had slipped out of the room and Rory jumped at the chance to chat in private. 

“Who, what now?” Lorelai wrinkled her brow, shoving a whole crab rangoon into her mouth.

“ _Careful,_ those are still hot. Jess, you know Jess! Bad-boy Jess. Bad-boy-turned-good-man Jess. _Jess Mariano_. He moved back to Stars Hollow.”

“He _what_!?” 

“ _Shhh!_ ”

“Does Luke know this?”

“I don’t know! Luke’s your ward! Ask your ward!”

“He was doing so great in Philly. Why would he come back here? Why wouldn’t he tell Luke? Why wouldn’t Luke tell me?”

Rory felt a wave of comfort knowing she wasn’t alone in her shock. If Lorelai had known about Jess’s return and not said anything, it would have felt like a betrayal. But it seemed like no one had knew. Come to think of it, maybe that was Babette’s favor–– to keep it a secret. 

“I have no idea. He just said the publishing business wasn’t going according to plan and he needed some time.”

“Some time?”

“Some time.”

Lorelai chewed slowly. She was wearing the Juicy Couture tracksuit pants Rory had bought her from a consignment shop on the Upper West Side. Leaning against the kitchen counter, head in hand, Lorelai barely looked a day over twenty-six herself. Rory thought for a moment how happy she was to be home. 

“He just got dumped.”

Rory snapped back to the moment, nearly yeeting the container of kung pao chicken in her hand across the room, “No way!” 

For some reason it hadn’t occurred to Rory that Jess had also been living his life over the last four, five years since they'd last seen each other. He had also been a free agent in the world––definitely meeting women, possibly falling in love, breaking up, moving on. He could even be married. She wracked her brain, trying to remember whether or not she’d caught a glimpse of a wedding band on his hand.

Lorelai tapped at her chin before taking a bite out of an egg roll. “Boy runs away from small town to big city. Boy experiences success. Boy meets girl. They fall in love. Girl realizes boy never resolved daddy and mommy issues. Girl dumps boy. Boy is forced to confront years of shit he has been diligently sweeping under the rug and realizes he needs to get the hell away to figure some stuff out. So, boy heads back to the only steady home he’s ever really had. Boy just hasn’t had a chance yet to talk to Uncle about it.”

Rory’s shoulder sagged. _Of course._ She was absolutely right. Feeling something strange stir in her stomach, she scooped only half of her kung pao chicken from the container onto a plate. “When you put it that way, yeah. That has to be it.”

“What has to be it?” Luke said, turning the corner with a laundry basket in hand. Lorelai’s face lit up and she immediately shifted herself to face him. _That’s what I want,_ Rory thought. It was an impulsive, uninhibited thought.

“You! It had to be you!” Lorelai quipped in a tight, old-time-y accent. A perfectly executed save, as always. 

Luke rolled his eyes but Rory could see he was hiding a smile. He set down the basket and grabbed his container of shrimp lo mein. “Ok, Frank Sinatra.”

“Ah, I should have known it was you making heart-healthy choices,” Rory chided, pointing at his shrimp.

“ _Yes,_ it was me. Unlike you titanium-made Gilmore girls, heart disease runs in my family and I can not eat endless piles of garbage.”

“How dare you refer to my most beloved kung pao platter as garbage!” Lorelai feigned insult, clutching at her chest. 

Rory felt her phone vibrate in her pocket. She pulled it out and tapped the screen till it blinked to life. Two texts. 

“Hey, I’ll be right back,” she said, but Lorelai and Luke were lost in their squabble over the merits of a fiber-rich diet. She pushed open the back door, clicking open the text. _Logan._

She and Logan had been broken up long enough for her to know not to expect anything romantic. Sure, they’d kept in touch and had even had moments together. Romantic moments, sexual moments. Moments of comfort and laugher. But that’s just what they were–– just moments. Barely strung together. 

So, why did it feel like her heart might burst out of her chest?

_Ace, you’re officially 26 in this part of the world. HBD. Live it up, xx_

HBD? Live it up? Sent at exactly midnight in London. What was he trying to get at, sending such a vague and vapid message at such a thoughtful time? _Typical Logan,_ Rory thought. A barrage of mixed messages that overwhelmed her physically and emotionally, leaving her more confused with each interaction that passed. 

And where was the second message? _I was promised two messages._ She clicked back and that’s when she saw it––an unsaved number from an area code that wasn’t New York, wasn’t Connecticut, and certainly wasn’t London. She hesitated, then opened the message. 

_Hey Rory, it’s Jess. Was great bumping into you. Figured I should text you from my new number so you have it. Coffee, don’t forget. P.S: Happy early birthday. P.P.S.: I liked your jeans. Are they from high school?_

She read the message, then read it again. Then again. She could practically hear his voice in the words. With a smile playing at her lips, she wrote back:

_Could never forget coffee. How bout tomorrow? Thanks re:b-day wishes and jeans. Yes, these bad boys are as old as our friendship._

For a nanosecond she considered deleting the last line. Were they friends? Did they really have a friendship? Before she could ruminate anymore, she hit send. Then, she took a few steps down into the freshly cut grass and plopped down. It was slightly damp, but close to the ground she could smell the freshness of the fall foliage and feel the coolness of the night air on her warm cheeks. All the houses around her glowed with the promise of full lives being lived behind their picture frame windows. 

Suddenly, she noticed the lightness in her stomach which, at some point, had replaced her usual anxious knots. 

She couldn’t quite place it but, sitting on her bum in her mom’s yard in Stars Hollow, Rory had a feeling twenty-six would be unlike any other year of her life.


	2. Part 1 - Damn Good Pie

**Summary for the Chapter:**

> It felt so easy talking to Jess. That was what had drawn her to him in the first place––their shared sense of humor, their love of books, their ability to banter non-stop, to exchange barbs and witticisms without ever missing a beat. He was so easy to talk to, she almost felt sad it had taken this long for them to reconnect. How many years had she spent nodding along to some dullard when she could have been doing this? Of course, there had been an unspoken factor in the equation before…
> 
> Jess and Rory meet for coffee. Split into two parts.

Rory slowed down to read the sign––Kelly Point Cafe. _This must be it_ , she thought, peering over the steering wheel out at the weather-beaten cottage painted a faded shade of lavender and sporting an enormous sign that boasted (in Comic Sans, no less) the Best Coconut Cream Pie In Connecticut. 

She came to a stop in the middle of the winding, two-lane highway that had taken her out of Stars Hollow, through the countryside, and to the edges of a close-by town. 

So, this was where Jess wanted to meet. 

_Interesting._

Rory’s birthday had passed in a haze of laughter, movies, Luke’s french fries, ice cream cake, whiskey gingers and a confirmation that she was indeed getting too old for that much sugar. She’d woken up early that morning, her second full day as a twenty-six year old, feeling like she’d been hit by a tractor trailer. 

“How are those wounds, soldier?” Lorelai quipped, greeting her in the living room with a mug so large it was essentially a flower pot filled with coffee. 

“Words loud. Talking hurt,” she grumbled, crumbling onto the couch. 

“Ah, yes, you’ve crossed over. You’re the age now where eating and drinking hurts and the only joys left are those experienced vicariously through the younger generation.”

Rory groaned loudly. 

“Kidding. Kind of. Not really.” Lorelai plopped down next to her on the couch, placing a hand on her daughter’s back. “The next thirty-six hours in Stars Hollow are all yours to waste away as you please. I’ll leave the keys to the Jeep on the kitchen table. The only thing you _can not_ forget to do––and in return you may destroy my home, bully Paul Anka, and terrorize Luke––is please drop by Sookie’s and thank her for the cake and cocktails.”

Rory just barely managed to lift her hand and form a thumbs up. “Sir, yes, sir.”

“Oh, and last thing––you left this downstairs.” She shoved Rory’s phone between her cheek and the pillow. “Damn thing wouldn’t stop vibrating. Tried to pawn it off on Paul Anka but he’s even more of a luddite than I am.” Lorelai stood and grabbed her purse while Rory forced herself to roll over and confront her phone. 70 texts, 10 missed calls, and 15 Instagram direct messages.

“O _y vey_.”

“Good luck,” Lorelei called over her shoulder in a sing-song voice as she made her way out the front door.

Rory powered through her brain fog and managed to delete 65 messages, all from a drunken group chat with herself, Lane, and Gypsy attempting to locate more late-night wine. Then there was a very long birthday text from Paris, which read more like a rambling note from Edgar Allen Poe than an HBD text; a picture text from Zach of Rory passed out face down in Lane’s lap; an all-caps happy birthday from her dad; and finally, a text from Jess. Her heart lurched when she saw his name. She clicked it open:

_Coffee today sounds great. Found a new place in Kelly Point that serves a decent cappuccino. Does 2 work?_

He’d sent the response at 6 am. _Typical,_ she thought. Jess was always an early riser––and a night owl. _And_ he always looked well-rested, now that she thought about it. She flipped open her front camera and cursed at the sight of her pale, dull skin and the purple bags under her eyes. A hangover usually meant laying in bed all day reading gloriously horrible 99-cent romance novels on her Kindle while very slowly eating a peanut butter and jelly sandwich. But something about the mental image of Jess going to bed late and rising early in his cabin made her write back with total confidence:

_Yep! See you then._

Aaaand that's how she ended up here. Pale, sweaty, and (for some reason) deeply nervous. 

Why the hell did he want her to drive all the way out to Kelly Point? There were plenty of perfectly good cappuccinos in Stars Hollow, none of which required transportation that actively made her want to puke. Rory could guess why. Babette’s unspoken favor: keep it a secret. 

She killed the engine and gave herself one last look in the rearview mirror. _Not bad…_ She’d managed to smooth her hair into a decent ponytail, and between some concealer and mascara, she actually kind of looked awake. She quickly applied some cream blush to her lips––and tried to not think too hard about why it was that she suddenly felt her lips needed to be a rosy pink––before getting out of the car and heading towards the cafe. 

It wasn’t really the type of place that screamed “decent cappuccino” and “Best Pie In Connecticut.” The pavement in front of the door was overgrown with weeds and the cafe’s windows were covered in years worth of grime and filth. Rory knew not to judge a coffee shop by its facade, but Kelly Point Cafe looked almost abandoned. It wasn’t until she was close enough to almost press her face up against the window that she could see inside. There were a few patrons at tables and a young woman bussing and waitressing tables. And there, all the way in the back, at a table in the corner, facing the overgrown forest that lined the highway, was Jess. 

Seeing Jess like that, the way a stranger would, made her insides feel like someone had pressed _eject_ on her stomach. He was undeniably handsome. In a classic way, like James Dean. His face was relaxed, even though his eyebrows were still knit together in a permanent state of contemplation. He was holding a book but not reading, and Rory softened at the thought of him daydreaming. Suddenly, it struck her that she would have given anything to hear the thoughts passing through his mind. Was he also nervous, anxious even, to see her? Was he thinking about Philadelphia, wishing he was back some place with more than two coffee shops? 

She pushed open the door and was immediately greeted by the waitress.

“Howdy!”

“Oh,” Rory blurted out. “Uh, yes, howdy.”

“You looking for a table for one?” she asked. The waitress was a short, little thing with a big, blond ponytail and playful green eyes. Rory couldn’t tell if she was being mocked. 

“No, actually, I’m with…” she pointed at Jess who’d snapped out of his daydream and was now smiling in her direction. It took all of her restraint to not knock over the waitress and barrel towards him. 

“Oh, you’re with _the writer_ , huh? Well, go ahead.” The waitress did a _thing_ with her eyes when she said “writer”––almost like a little dance. The nickname nearly triggered Rory’s gag reflex. Furrowing her brow, she thanked the waitress and made her way to the table. 

Inside, the cafe was actually really nice, decorated with retro surfboards and vintage Coca-Cola signs. Classic and inviting as it was, Rory was already experiencing the urge to shout, “Fifteen minutes down the road there’s even better coffee, _I promise!_ Drop your cappuccinos and we ride!” 

Jess broke into a grin as she made her way through the tables. 

“Birthday girl,” he called as she got closer. 

Rory slid into the chair across from him. “Kelly Point, huh?”

Jess immediately looked a little chagrined. “What’s wrong with trying something new?”

“Nothing at all, I’m just still working through the shock of being greeted with _howdy._ ”

Jess laughed, “Liza’s a nice kid.”

Rory’s stomach dipped like she’d missed a step. “Liza, huh? I could have sworn her name was Pippy.”

“Impossible. Pippy had red hair,” he quipped in response, leaning over to pull something out of his messenger bag. “Don’t freak, but I got you a little something…” He rolled his eyes, attempting to fight off a smile. 

“Oh, Jess. You shouldn’t have. Seriously,” she said. But he’d already pulled a neatly wrapped rectangle and placed it on the table between them––all wrapped up in brown paper, tied with a single piece of twine. 

“Go ahead, open it.”

Rory bit her lip and slowly took the package between her hands. She felt its thickness and slight give when she squeezed the mystery object between her hands. _Of course,_ she thought, _it’s a book._

“Jesus Christ, just open it. You’re killing me!” he laughed.

“Sorry, sorry. I tend to get a little sentimental…” she grinned and began tearing away the paper. 

She gasped; a hardcover copy of Anthony Bourdain’s Kitchen Confidential––and it was signed. 

“Jess, this is _perfect_.”

“Yeah?”

“Yes! It’s perfect! How did you know? I just started a job with a food magazine and at first I was feeling kind of down about it––who am I to write about food, you know? So, I’ve been reading everything I can get my hands on––”

Jess was actually grinning now. A huge smile, spread across his face.

“What?”

He shook his hand and fiddled with his mustache. “Nothing. I’m just happy you like it.”

“I can’t wait to read it––”

“Can I get you two kids anything?” It was the waitress again, standing over them with a notepad, a pen and a look that Rory couldn’t quite place. 

“Just a black coffee for me, please.” 

“And I’ll do a cappuccino and a slice of the coconut cream pie.”

After the waitress was out of ear shot, Rory leaned forward. “The best in all of Connecticut, huh?”

He scoffed, “You better believe it.”

It felt so easy talking to Jess. That was what had drawn her to him in the first place––their shared sense of humor, their love of books, their ability to banter non-stop, to exchange barbs and witticisms without ever missing a beat. He was so easy to talk to, she was almost sad it had taken this long for them to bump into each other. How many years had she spent nodding along to some dullard when she could have been doing _this_? Of course, there had been an unspoken factor in the equation before… 

“You wait until I tell Luke you said that,” Rory said, testing the waters on her Babette theory. 

Jess’s smile fell a bit. He cleared his throat and dropped his voice to a whisper, “Yeah, about that. I’m not actively keeping it from Liz and Luke that I’m home––” _Here we go,_ she thought. _The truth_. “––but I’m kind of steering clear for the time being. Only heading into town after he’s closed up the diner or not working, et cetera. It’s just… I don’t want Luke to get the wrong idea.”

“And what would that be?” she asked, matching his low tone. 

“That I went and fucked everything up. That I stormed off and quit Truncheon, or ruined a good thing while I had it.” He made a face like it wouldn’t be the first time Luke had spoken to him about the latter. “I know what you mean. Luke can be a little…”

“Explosive? Impatient? Reactionary? Harsh?” 

Rory laughed, “Your words not mine. I love Luke, but I get it. Your secret’s safe with me.” 

“Thanks, I figured I could trust you.”

“So, if you didn’t fuck it all up…”

Jess chuckled, “Fine, yeah, I guess I owe you my sob story.” 

Those words made her mouth go dry. She stayed quiet and let him continue.

“Where do I even start? Three years ago I started dating this friend of a friend––Nia. She was a graphic designer who did some cover art work for us and… she’s so beautiful.” _Dammit, Lorelai Gilmore,_ Rory thought. _Always right._

“I just fell for her. Immediately. She was funny and goofy and has this great, big smile. She made me feel like I could relax, like I could just be calm. I hadn’t felt that way in––” he paused suddenly and flicked his eyes up at her. “Well, it had been a while. So, we started hanging out. Dating. Next thing you know she moves into my place, brings her cat, Buckles. Bad name but a cool cat. Everything feels perfect at this point.”

Rory pulled her sleeves over her hands and folded her arms awkwardly, “You’re not convincing me you didn’t fuck something up here, Mariano…”

“She cheated on me,” he blurted out. “With Chris.”

Rory felt all the blood drain from her face. _This_ was something she had not seen coming. “Jess...I-I’m so…”

“Yeah. I leave my bike helmet in the office after working for, like, twelve hours. I head back to grab it and who do I catch Chris rolling around the printing room with? Nia.” He shook his head and paused before saying, “Want to know the worst part?”

“It gets _worse_?” 

He leaned forward, pronouncing each word carefully, “I felt nothing.”

She stared at him, dumb-founded. “But...Buckles…”

“I felt nothing. It was the scariest feeling in the world, Rory. This girl––woman––who I thought would marry cheated on me with one of my best friends, my business partner.”

“Your _best friend._ Your _business partner_.” 

“And I felt… fine.”

“You’re in shock. You’re grieving.”

“No, I’m not.”

“You’re in denial. You’re in so much pain, you don’t even know it.”

He shook his head. “No, I’m not.”

“You’re falling apart! You’re being destroyed slowly, one cell at a time, by all consuming sadness!”

Jess laughed, “No. I’m not.”

“Pie,” Rory said flatly. 

“What?”

“Pie’s here,” Liza confirmed placing a plate between them, followed by their coffees. The pie was buried, somewhere, under an enormous pile of whipped cream. Rory grabbed a forkful, shoving it in her mouth. 

“I’m having some of your pie. I need some of your pie. Without pie, I can’t even think right now.”

“You’re telling me. I’m the one who lived it. So, I asked her–– _kindly_ ––to move out before the end of the month. Told her I’d get out of her hair until then.” 

They both chewed for a moment. The pie was really _so_ good. The crust was flakey and buttery, the filling velvety smooth and nutty with a hint of honey; sweet but not too sweet.

“Damn,” Rory said, finally breaking their silence. “That is some damn good pie.”

“Told you.”

“You really think Luke won’t listen? If you tell him everything, you really think he won’t get it?”

Jess shook his head, “If I was a broken up mess, sure. But right now, it’s too complicated.”

“How is it complicated, Jess? She cheated on you. She took your relationship and tore it apart.”

Jess stayed quiet for a while, stirring his cappuccino, breaking up the carefully designed pattern in the milk. 

“Because I could have gone anywhere. But I chose to come here.”

She raised her eyebrows, “Ok, so?”

“There are just some things I need to resolve…” His gaze drifted away, out the window. While Rory’s anxiety had been replaced by genuine worry and concern, his shift in mood suddenly gave her goosebumps. She took a long sip of coffee, aware of the blood pulsing behind her eyes. She was, no doubt, starting to turn red.

“Ok...Like what?”

He took another bite of pie, chewed slowly, wiped his mouth and set down his napkin. An eternity seemed to pass before he finally said it. 

“Us.”


	3. Part 2 - Choices and Chances

**Summary for the Chapter:**

> “It was really great to see you, I wish I didn’t…” She stopped, biting her lip.
> 
> Jess smiled solemnly, kicking at a rock. “It’s ok, I don’t expect you to feel the way I do. I’ve had a lot of time to unpack this,” he paused, exhaling a deep breath. “And I promise by the next time you’re in Stars Hollow for Halloween or Autumn Festival or whatever, I’ll be gone,” he said while locking eyes with her. “This isn’t going to be like before. I promise. This is it.”

**Notes for the Chapter:**

> Had a bit of writer's block after posting twice in one week! Going to try my best to keep up that pace with two chapters a week, but I am still shaking off the cobwebs :) Please comment/share/bookmark/leave kudos if you enjoy.

Rory felt as though every single cell in her body simultaneously vibrated. A dull ringing filled her ears and her stomach twisted like she was falling ass-backwards down a mountain. Hands shaking, she grabbed onto her coffee mug for something, anything to make her feel grounded. 

“Us?” she asked. Rory hadn’t even realized there still was an “us” when it came to her and Jess. She’d been nervous to even mention _friendship._

Jess nodded slowly, “Believe me, I wasn’t going to say anything. I don’t want you to think I invited you out to coffee so I could corner you or something. But my therapist…”

Rory nearly spit out her mouthful of coffee, “Your _what?!_ ”

Jess’s eyes widened in amusement, “Yeah, yeah. Little ol’ fuck-up Jess Mariano in therapy.” 

“I think I may need more pie…” Rory said, rubbing her temples. 

The Jess sitting before her was like a hologram; depending on which way he shifted she caught a different version of him, changing so subtly yet so quickly it nearly knocked the air out of her. He was still charming and witty, but he was kinder, softer around the edges. He always listened well, but now he really looked at her when she spoke, with empathy and interest. He was still the guy who so many times had disappeared and reappeared in and out of her life with big, sweeping statements and gestures. Crashing into her like a hurricane or tornado: turning up suddenly to tip over tables, break some windows, and stun her. But now he had a _therapist._

“Sorry, I didn’t mean to shock you to the point of needing to dull the pain with pie. I didn’t even think this would come up…” He looked chagrined, “I promise.”

“No, c'mon Jess. It's me. I’m just surprised you found time between bull fighting and being an aficionado to find a therapist,” Rory said. 

“Hey, I already told you. I’m not a Hemingway, I’m a Stephen King,” he smirked at her. 

She laughed then asked, “What did your therapist want you to tell me?”

Jess cleared his throat and began fiddling with his fork, pushing around the last few crumbs left on the plate between them, “He pointed out that maybe with Nia, having everything go so well, I was experiencing some ‘latent guilt’––” he flitted his eyes up towards her and she could see an edge of embarrassment creeping into them, “––over how I treated you. Taking out so much of my anger and frustration on you. Disappearing. Showing up again. Pissing off _your mom_ ,” he shook his head gravely at how stupid he’d been. “I wanted so badly for us to work, Rory,” he smiled sadly. “And I fucked it up every chance I had.”

Rory almost pinched herself to confirm what was happening was _really happening._ How many times had teenaged Rory imagined this moment––a moment of reckoning with the one guy who seemed to know her better than anyone and could hurt her more than anyone? 

He had been the first guy she’d ever dated to show her that books didn’t have to be just something she enjoyed––they could be her whole life. And writing didn’t have to just be her escape, her career. It could be something she shared with someone else, someone who also loved writing as much as she did. The truth was she’d already forgiven Jess––she had to. It was Jess. There was no one else like him in the world. She’s sealed off the hard, bad memories of their time together and marked the box as “Fragile - Do Not Open” and moved on. 

_Life,_ Rory thought, _is about choices. And we both made choices._

“Jess, we were kids.”

“So? That doesn’t change the fact that I hurt you.” 

“We saw each other a few years ago and everything was fine.” 

This made them both laugh, slicing through the tension like a hot knife. 

“Was it?”

“Ok, no. It wasn't fine and that was my fault,” she rolled her eyes, cheeks burning as she remembered their kiss and the horrible embarrassment that followed. “See? I hurt you too. But still, I was happy to see you then.” He flicked his eyes over to her again and this time their eyes met. Her stomach felt like it was suspended inside her and for a moment, she forgot to breath. “And I’m so happy to see you now.”

Jess smiled and took another incredibly long pause before saying, “Rory, I still have feelings for you.”

She nodded slowly. _Jess Mariano. Feelings for me_. 

“You don’t have to do anything or say anything. I came back here because I have to figure my shit out.” 

Before Rory could speak, her phone buzzed. A reminder popped up on the screen: _GO TO SOOKIE'S!!!!!!!!_

“ _Shit._ I almost forgot. I have to get back to town––I have to thank Sookie for the cake and the cocktails. My mom will literally kill me if I don’t do this one thing for her.”

“No problem, I understand––”

“Shit!” Rory yelped, “It’s almost five! Ok, I really have to go…” She grabbed a wad of cash from her wallet and dropped it on the table, “Is that enough for pie?!”

“Geez, money bags, maybe in the Swiss Alps. Take back one of those tens and let’s get out of here.” 

He walked with her to her car, taking slow, long steps with his hands shoved into his pockets. Outside Rory began shivering in the early evening air. The sun was almost all the way set and a chilly breeze stirred the trees that lined the road and hung above them. 

“Thanks for grabbing coffee with me,” Jess said, staring off at the highway behind her. He was standing so close she could feel warmth radiating off his chest. She ran her eyes over his face and tried to imagine how Nia had felt, being with him for so long. Three whole uninterrupted years. Her brain was a twisted mess of thoughts, none of which she could pull apart. “And thanks for listening.”

“It was really great to see you, I wish I didn’t…” She stopped, biting her lip.

Jess smiled solemnly, kicking at a rock. “It’s ok, I don’t expect you to feel the way I do. I’ve had a lot of time to unpack this,” he paused, exhaling a deep breath. “And I promise by the next time you’re in Stars Hollow for Halloween or Autumn Festival or whatever, I’ll be gone,” he said while locking eyes with her. “This isn’t going to be like before. I promise. This is it.”

He opened the car door for her. “It was really great to see you, Rory.”

Rory swallowed hard, pulling her gaze away from his. She hesitated before getting in. _Say something, Gilmore, anything_. 

But nothing came. She got into the car and began to back out of the lot, and as she headed back down the country road that had brought her to Kelly Point, she looked back in her rearview mirror. 

There he was, on the side of the road, watching her drive away. 

~*~

When Sookie pulled open her front door the last person she expected to find standing there with tears streaming down their face was Rory Gilmore. 

“ _R_ _ory!_ What the hell happened?”

Rory took an enormous, shaky inhale before launching into a breathless ramble. 

“I was supposed to come here to thank you for the cake and the cocktails. But I bumped into Jess. Yeah, Jess. _That Jess_. Jess Mariano. And we got coffee and it was great and we were laughing and talking about all sorts of stuff and then he told me he’s back here because he’s going through something. And stupid me was like, _tell me more, please, I’m an idiot_ . And it turns out he has feelings for me? And, and I’m supposed to be a writer by now but all I have is stupid job for a magazine about _spaghetti._ ”

“Damn it, Jess,” Sookie cursed. “Come on in. I can’t have you crying on the porch, the neighbors will think I’ve been bullying vendors again.”

Sookie grabbed her by the wrist and pulled Rory into the house where she was immediately hit with the warm, fragrant smell of tomato sauce. 

“Don’t mind the smell,” Sookie rolled her eyes, “Jackson’s making two gallons of amatriciana sauce––he lost some bet to a Roman zucchini farmer.” 

Rory flopped down on the couch and, faster than she could dry her eyes, Sookie reappeared with two glasses of chardonnay.

“Does your mom know?”

Rory shook her head, “Only that Jess is in town. I didn’t tell her I was meeting up with him-- and get this, he didn’t tell Luke he was in town either. He kept saying he didn't want people to know, didn't want to make a big deal. He doesn’t want any hoopla. He just wants to...heal.”

Sookie’s eyes grew approximately two inches in diameter, “Heal?”

“He has a therapist.”

“Like a physical therapist?”

“Like a brain therapist.”

Sookie took an enormous gulp of wine, swallowed hard, then said, “People can change. People change all the time.”

Rory shook her head, “Jess was always good. I always knew he would be good, once he figured everything out, you know? I just never thought figuring things out would mean he’d end up back here…” she swirled the last bit of wine in her glass before throwing it back. “He had a girlfriend. For three years.”

Sookie chuckled, “Sweetie, you almost had a fiancé.”

_Ouch. Right. Logan._

“Sookie, what do I do?”

She sighed and placed her wine glass on the coffee table. “You go home. You take a bath. You sleep for twelve hours.”

~*~

_They’re on the road in front of Kelly Point Cafe. A thick, white fog has drifted in from the lake and settled around everything. All of the lights are out except for one-- a single streetlamp. In the distance, she can see him. Jess. Standing alone under the streetlamp._

_Jess! Rory calls out to him. Is that you?_

_He smiles and starts walking towards her. He’s only a few feet away now, getting closer. Suddenly, there’s a glitch. A technical schism. The air around him warps and fragments into pixels, tiny squares of blinding light. He disappears, then reappears back to where he started. Under the streetlamp._

_Jess! Rory shouts. What’s happening?_

_He smiles again and begins walking towards her. Closer and closer. He’s only a few feet away now._

_Jess, how did we end up back here? I thought you said you’d be gone… Rory is almost screaming over the sound of the wind. Has it been blowing the whole time? Rory can’t remember but it’s blowing so loudly now it sounds like a train whooshing past. And yet nothing is moving. The trees are still. Jess’s hair is perfectly placed._

_Can you come closer? I’m having a hard time yelling over the wind, she shouts_

_He smiles flatly, his eyelids heavy and his eyes distant--no nod, no wave. Again, he starts walking towards her._

_Jess! Stop! Stop right there! It’ll happen again-- the thing with the light. Hold on, I’m coming to you._

_But as hard as she tries to run, she can’t move. And as hard as she yells at him to stop, he doesn't stop. He keeps walking, keeps glitching-- his skin dissolves more and more each time, until he's nearly gone. Disappeared. Rory keeps shouting louder, but her voice only fades into the wind. Still, she tries shouting, forcing her voice out until it hurts, until the wind filled her lungs, over takes her voice, choking her slowly…_

Rory shot out up in bed, gasping. 

“Air!”

Paul Anka popped his head up from his place on her floor, staring at her in exhausted annoyance. 

“A nightmare. Just a nightmare,” she mumbled, breathless. She inhaled as deep as she possibly could. No wind here. _It was all just a horrible dream._

She reached over to the nightstand and felt around till she found her phone, tapping the screen to life. No messages. 

Why had she thought there would be any?

She flopped back on her pillow, grateful for the gentle breeze coming in through her window and cooling her face as she replayed the image of Jess disappearing over and over, leaving her with a metallic, sick taste in her mouth. 

~*~

“Good morning, Vietnam. Or should I say Captain Willard? Sounded like there was an apocalypse happening down here,” Lorelai quipped, pouring herself a mug of coffee with one hand and shoving bread into the toaster oven with the other.

Rory sat at the kitchen table, a worn copy of Anna Karenina open in front of her. She’d been up since 5 am, attempting to clear her mind with a familiar read, trying to think about anything and everything except yesterday. She rubbed her eyes, “Thinking about Francis Ford Coppola this early is _almost_ as bad as the nightmare I had last night.”

“A nightmare, eh?”

“Yes, a nightmare. I can’t even begin to explain how weird it was to you--”

“Good morning,” Luke announced, sweeping into the kitchen in a cloud of aftershave. He gave Lorelai a peck on the cheek. “You’ll never believe who I just heard from.”

“Who?” Rory asked at the exact same moment Lorelai said, “George W. Bush and he’s very sorry.”

Luke rolled his eyes, “Jess.”

“Oh,” Rory and Lorelai said. Only one of them sounded unconvincingly surprised; Rory shot Lorelai a look. 

“Yeah, unbelievable. Said he’s in town for a week for work or something and he wanted to swing by the diner first thing today, before it opened.”

Rory felt her stomach drop -- _I’ll be gone._

Luke looked around sheepishly, “I’d invite you both but I figured...”

“Jess and I are fine. We’re friends.”

“I’ve made _so many_ more enemies since 2002. But go ahead and enjoy your manly alone time, as men. You guys can grunt and stare approvingly at each other without our soft, feminine judgement.”

“Judgement-free man time,” Rory echoed her mom, grateful she’d found a way to finesse the conversation without Luke noticing. 

“Alright, alright,” Luke laughed, grabbing his keys and heading for the door. “Can’t promise we won’t lose ourselves in each other’s eyes.”

Rory grinned at Lorelai, “He’s started doing bits with you!”

Lorelai placed a hand over her heart and blinked back fake tears, “He has. After all these years.”

The toaster oven popped and Lorelai grabbed her breakfast, settling in across from Rory. “Now that Luke’s gone, are you going to tell me about this nightmare? And possibly elaborate on why you were moaning Jess’s name in your sleep last night?”

For the second time in two days, Rory nearly sprayed someone with a mouthful of coffee, “I did _what?_ ”

“Uh, yeah, kid. It was disturbing. I’m not talking sexy moans–– _thank God_ ––but more like…” Lorelai screwed her face up in agony and recreated a guttural warbled shout, “ _Jeeeessssss!_ ”

Rory slammed her book shut and covered her face with both hands, every part of her burning with red-hot humiliation, “Dammit, dammit, dammit.”

“Aw, I’m sorry, I didn’t mean to embarrass you.”

“Why are _you_ sorry? I’m the one waking up the whole neighborhood, shouting my ex-boyfriend's name in my sleep!”

“Yeah, I had to check my calendar and make sure we were still in the 2010s. Are you okay, kid? Did something happen?"

She lowered her hands, “If I tell you, do you promise-- _promise_ \--not to tell Luke?”

Suddenly Lorelai’s playfulness was replaced by her mom look. With eyebrows furrowed and shoulder hunched, she reached across the table for Rory’s hand, “Of course.”

~*~

Lorelai's advice had been simple: go back to New York. Give Jess what he wants. Let him figure everything out. 

But as Rory sat back in her train seat, the Connecticut countryside whizzing past her, she couldn’t shake the solid feeling in her stomach that this _couldn’t_ be the last time she saw Jess––not ending with those words, not after that dream. How could she let it end like this? 

It wasn't just about Jess. Not really. For so many years everything in Rory’s life had felt perfectly organized--Chilton, Yale, Logan, her work on the campaign trail--until it suddenly wasn't; until everything opened up into a big, wide, boundless sea of choices and chances. And what had she done? She still fooled around with Logan, but she never dated anyone new-- not for very long, anyway. She worked at a few magazines and newspapers, but had she really taken big risks, put it all on the line for a real staff position or a story that could make her a household name?

 _Am I always supposed to stay this small?_ Rory thought, angrily, _Always living in the shadow of the past?_

It didn’t seem fair. But it didn’t have to be that way. What if this time things really were different, not because they walked away but because they ran towards each other? 

_Choices,_ she reminded herself, _we all make choices._

She yanked open her purse and pulled out a piece of paper from her spiral notebook. Using the only crappy pen she had in her bag, she wrote at the top: _Jess Mariano_ \--an action that made her stomach feel like it was infested with butterflies--and in clear block letter beneath she wrote “PRO” and “CON”. 

She had to make a choice.


	4. The Jess Question

**Summary for the Chapter:**

> Her tears splashed against the page, causing the ink to run. Hands shaking, she tore up the paper until the pieces were too small to shred anymore. Then she tossed the pieces into the air, over the water, sending her hopes and fears and dreams swirling into the sky. They floated away, almost like snow. 
> 
> Enough. 
> 
> She pushed forward into the night. The tears had stopped falling now but her hands trembled. Every muscle in her body quaked. From fear or anticipation or maybe freedom. She knew what she had to do. 
> 
> She pulled out her phone and wrote the text. 

The trees in Central Park were a shimmering, fluttering mass of gold and orange, and all around Rory the city bustled with the relief of the brisk early fall air. Tourists lined up down the block for a churro from the cart right outside Central Park. A bellhop ushered a full trolley of luggage into The Plaza. A small group of protestors shouted in unison outside a restaurant. No matter how Rory had woken up that day, her morning walk down Fifth Avenue to Central Park always made her feel alive. 

Every morning Rory took the M train from Williamsburg into the city an hour before work. Then she bought an enormous 24 ounce coffee from her favorite bodega in Midtown and walked the entire length of Fifth Avenue until she hit Central Park, where she sat and read for an hour on her bench. Yes, it was her bench. Just close enough to the street that she could hear the cars passing and people yelling, but just tucked away enough that in the summer she was shaded and in the winter she had a reprieve from the wind. 

It wasn’t lost on Rory that maybe she was better at picking reading spots than she was choosing men or jobs. And this morning she wasn’t as eager as usual to get to her spot, knowing that her book could only do so much to take her mind off of everything that had happened just a few days earlier. Like a lead brick in her pocket, the Pro/Con list she’d written on the train back last night seemed to physically pull her down. She’d spent the entire train ride frantically scribbling away, letting the thoughts flow from her before the rational part of her could intercept. It was long––longer than she’d thought it would be––filled with the unending anxieties that had followed her since the day Jess Mariano had taken his car and peaced out. 

Ten years of untouched feelings. When she’d finally finished pouring herself out on the page, she’d taken a deep breath and with a flourish written, “The Jess Question” at the top of the list. 

Like all of her writing, she had to give it a good title. 

No sooner had her butt touched the bench, her phone buzzed. _Was it––?_ No way. He wouldn’t. _He said he would be gone._ Heart pounding, Rory pulled her phone from her pocket. 

It wasn’t Jess. No, not at all. In fact, it was the literal opposite of Jess. 

Logan. She opened the text: _Ace, in town tonight for a meeting. Dinner at Boucherie? I know you like their frites. My treat, birthday girl._

“Jesus Christ _,_ ” Rory hissed under her breath. What was it about twenty-six that had every man from the last decade of her life tap-dancing back for a round two? Though Logan was different. It wasn’t uncommon for them to meet up for a rendez-vous every time he had a layover in the city. There was no confusion or miscommunications over what this was: an elaborate but polite booty-call. A quickie while he waited for his flight back to London, punctuated on either side by charming conversation, passive-aggressive commentary, and a lot of champagne. Sometimes there were sweet-nothings murmured, but only after the champagne and not a moment sooner. A wholly unhealthy encounter that never failed to leave Rory feeling _bad_. The Pro/Con list in her pocket seemed to actually throb now, reminding her of her promise to make better choices. Stronger choices. Better choices. She took an enormous sip of her coffee, throwing her head back like a wine-o at the bar. 

_Is this really what I want?_ Rory thought, guilt playing at the end of her mind as her thumbs hovered over the keyboard.

 _But... steak frites._

And just like that, she wrote back:

 _You’ve got my number. Can’t say no to anything that is French and fried,_ she fired off

 _Cool see you there at 8,_ he responded almost immediately.

Rory dropped her phone in her lap and immediately put her face in her hands. 

She’d brought Kitchen Confidential, but suddenly her appetite for a good story was gone. 

~*~

“We’re light on topics this month, people! You know this is not how I like to live my life,” bellowed Greenwald as he slammed the door to the conference room closed. Sebastian Greenwald was senior staff editor and Rory’s boss. Everyone called him by his last name— Greenwald; a hangover from the good old boys days of New York journalism, a tradition that simultaneously enraged and enchanted Rory. She felt like she had a real paper job, complete with the nepotism, ageism, and sexism.

Rory began flipping through her notebook. She always kept a running list of feature ideas for moments like this. 

“We could do Best Dollar Slice in The City again,” called out an intern with thick horn rim glasses and a pretty sleek unibrow; they called him Eyebrows.

“Yeah, or we could do something edgy, like Best Place To Go On A Bender,” someone else shouted. 

Greenwald kept pacing, “Way too done, Eyebrows. And you, not done enough and for a good reason. Jesus, people. _Think_ about our demographic.” Rory kept flipping through her notebook. _Dammit_ , she thought, _gotta be something here._ She knew the demographic like the back of her hand. She knew everything about their small but loyal audience. Stay-at-home Manhattan moms! Single women in their mid-30s! More likely to drive an eco-friendly car! 

“I almost feel like we need to be thinking bigger than New York.”

Just like that, it hit her. “What about Connecticut?” she called out, causing heads to swivel in her direction. “I just went to some place that claimed they had the best coconut cream pie in the whole state.”

Greenwald froze, shifting on his heels to face her. 

“Tell me more, uh…” he snapped his fingers a few times. 

“Gilmore. It’s this shack on the side of the road in Kelly Point, Connecticut. It’s so kitschy, they use Comic Sans for all of their signs and menus. And their pie was actually so good—maybe the best I ever had, now that I think about.”

“I _love_ this,” he shouted, causing Eyebrows to jump in his seat. “A great filler piece. Some fluffy Americana we can use to pad the main profile and all the pumpkin spice recipes. Right, can you get me a 500 word pitch by tomorrow morning?”

A grin spread across her face, “Yes, sir.”

Eyebrows glared in her direction. 

~*~ 

Between slugging coffee and proofreading her report, Rory had no time to catch the subway home and back to Manhattan in time for dinner. It was better that way. The distraction was more than welcome. She’d spent the few moments of free time she’d had that day to talk herself out of cancelling on him. It didn’t mean anything to get dinner with Logan when Jess had essentially promised he was fading into the sunset, she told herself. No matter the outcome of her Pro/Con list, there was no telling whether or not Jess would change his mind if she reached out. And who even knew what Logan wanted? Maybe it really was just dinner. 

_Yeah right,_ she thought. 

Early for their eight o’clock reservations, Rory stood outside Boucherie, using her phone's camera to apply a quick coat of red lipstick. 

“Well, well, well, if it isn’t the prettiest twenty-six year old on the island of Manhattan,” a voice crooned from behind her. She jumped, nearly veering out of the lines with her lipstick. 

“ _Jesus_ ," she gasped. "Huntzberger, can't you be wary of an old man’s heart?”

He grinned and held his arms open, “Ace.”

She moved immediately into his arms. He lowered his lips to her neck and his hands wandered down her back to her hips. She’d forgotten about this part-- the easy, familiar intimacy they fell into with each other. Such a vivid contrast to Jess who seemed to move around her with caution. Logan held onto her like he knew she wouldn’t say no. And he was right. For this moment, he was totally right. 

She let herself melt slightly into his embrace--something she hadn’t felt in a while. It felt good just to be close to someone. 

“Okay, I think I’ve had enough steak in my life, how about we go back to my place?” he said.

“Hate to break it to you, but I’m here for my biannual expensive plate of french fries,” she laughed, pulling away, breaking the spell that had momentarily come over her.

He looked great––his skin was smooth and dewy, his blonde hair perfectly tousled, and his European sports jacket the perfect shade of green to make his hazel eyes pop. His eyes played over her body and, still holding on to her hands, he pulled her close to him again. 

“That’s fine, I can handle being second in your life,” he quipped. 

She pulled away, screwing her face up, “I’m sorry, were you under the impression that you're first in my life?”

He rolled his eyes, “I’m kidding, Ace.”

She pulled her hands out of his, pulling her jacket closed. “Got it. Jokes. Always tricky to identify, aren’t they?”

“Aw, c’mon, don’t be that way,” he said, yanking the door to the restaurant open. “We’re here for a good time, not a long time.” She rolled her eyes, but couldn’t help but smile. He was right––it was all jokes, it was all kidding. By tomorrow morning, he’d be back on a plane and out of her life. 

Walking past him through the doors, a creeping sensation came over her. By tomorrow he’d be gone. How many more people were going to tell her that? Was that her destiny, to always be alone? She pushed the thought away. _Not now._

Inside the restaurant was alive with plates clattering, glasses clinking, people laughing and the wonderful smell of steak being cooked to perfection. Logan raised a hand to the hostess and guided Rory up a set of steps to a mezzanine with white tablecloth covered tables. 

“Have an in with the hostess, huh?” she said. 

“The Huntzbergers love a good croquette de jambon, so we spend a lot of time here.”

Rory fought with her entire soul to not roll her eyes. _Of course they do._ Rory and Logan couldn’t go anywhere in this city without something or someone or somewhere triggering a story about the Huntzbergers. _What would Jess think?_ Rory already knew, no need for that thought experiment. He’d remind her that a croquette de jambon was just a rich man’s ham sandwich and he’d call Logan an entitled bastard. The thought made her smirk. 

They slid into their chairs at a table that overlooked the entire restaurant below; a waiter quickly came with glasses of water, nearly bowing for Logan. 

“Can I start you off with anything to drink?”

“I’ll have your best rye whiskey, neat, and whatever the lady wants,” Logan said. 

“I’ll have a gin and tonic, please.”

The waiter took the order and seemingly vanished. 

“No wine?” he asked.

“Wine gives me a headache and I have to be at work early tomorrow.”

He raised his eyebrows, “And where’s work these days?”

Rory dreaded this part, absolutely hated it. She bit her lip, her stomach rising in her throat. “A food magazine, maybe you’ve heard of them. It’s called Relish.”

He smirked, “Cute name.”

“They’re quite reputable within their key demographics, actually.”

“And who’s that? Their other friends on the fridge door?”

Her blood pressure surged, “Another one of those hard-to-spot jokes you’re fond of.”

His smile softened, “I’m kidding, Ace. That sound awesome, I’m really proud of you.”

She scoffed, “I don’t need you to be proud of me.”

Shock washed over his face, but before he could respond the champagne and cocktail arrived. Rory sipped down her entire gin and tonic in one shot. 

“You were thirsty.”

“Parched.”

“Waiter?” Logan raised a hand, waving the waiter back over. “Another gin and tonic, please.”

He seemed to be challenging Rory, maybe even mocking her. 

“You still living in Brooklyn?”

“Yes, why? Do you have something to say about that?”

He laughed, “Relax, Ace––”

“Don’t tell me to relax,” she shot back. 

He stared at her, his eyebrows knitting together in angry concern. “What is wrong tonight? Seriously, did I do something? You’ve been acting weird since the moment we saw each other.”

“No...No, sorry,” she rubbed her face in her hands, careful not to smudge her lipstick. “I’m not feeling well, it’s been a weird week. I’m just confused. Mixed up.”

“About…?”

“This. _Us._ Logan, what are we even doing?”

He licked his lips slowly. “We’re old friends getting dinner.”

“Why?” she pressed, “I don’t mean to be rude––you know I appreciate you and our friendship. But is this really something we should still be doing? Dinner and sex twice a year?”

Logan stared at her blankly, “Do you want something more?”

“N-No, I––”

“Because I did try that, Rory,” he said, his voice raising ever so slightly. “I did ask you to marry me. Do you remember that?”

She exhaled, “I know…”

“So, forgive me for wanting to keep you in my life despite that rejection.”

Rory let the pain of the moment wash over her. She took a long sip of her drink. “Are you seeing anyone right now?”

Logan swallowed, flitting his eyes towards the people below them. “Yes.”

“Do you love her?”

Silence. Logan kept his gaze far away, refusing to meet her eyes. Below Rory could hear a table loudly singing happy birthday. Far off, a plate shattered and a group erupted in laughter. _People living life._

Rory spoke first, “Logan, even if you don’t love her… I just… I don’t think we should do this.”

He stared at her, a multitude of emotions working their way over his face. Anger, sadness, pain, disgust. She saw it all play out before her. Tears sprung to her eyes, “I’m so sorry.” 

~*~

The wind was vicious outside, blowing a mix of trash and leaves up and down the empty block. The city was eerily quiet, adding to the nausea Rory felt. She pulled her jacket tight and began walking as fast as she could, letting the wind propel her forward. Part of her was afraid Logan would try to chase after her, but another part––a bigger part–– knew they were way beyond that. 

He didn’t love Rory, he didn’t need Rory; he’d clung to Rory because she was the last vestige of rebellion in his life. A common girl from a common family. The last middle finger still raised in his life. The tears fell down her face, uninhibited. It was the truth she’d been avoiding, the one that caused the most pain _._

She’d needed to do this for too long, but she’d let their relationship keep going, unchecked, regardless of how it impacted others let alone herself. She was at the Brooklyn bridge now, the entire city lit up behind her. The moon was hanging full and low in the sky, reflected perfectly on the Hudson. She slowed her pace, letting a few sobs. Finally alone, she let herself cry as she walked. Midway across the bridge she pulled out the list.

_PRO: Same taste in music, Same taste in books, Always believed in me, Always loved me for me, Supportive, Thoughtful, Loyal, Sexy…_

It went on and on and on. 

_CON: What if he leaves?_

She stared at the page. _What if he leaves?_

Fear had blocked her so many times––fear of failure, of success, of being who she was meant to be. She was sick of fear––done with it. Rory Gilmore got what Rory Gilmore wanted. Her tears splashed against the page, causing the ink to run. Hands shaking, she tore up the paper until the pieces were too small to shred anymore. Then she tossed the pieces into the air, over the water, sending her hopes and fears and dreams swirling into the sky. They floated away, almost like snow. 

_Enough._

She pushed forward into the night. The tears had stopped falling now but her hands trembled. Every muscle in her body quaked. From fear or anticipation or maybe freedom. She knew what she had to do. 

She pulled out her phone and wrote the text. 

_I don’t want you to be gone._

After hitting send a swell of energy overcame her. Practically jogging, Rory took off into Brooklyn towards her apartment, the brownstones and fluorescent bodegas whizzing by. She wasn’t sure why she was running, but something inside her told her to keep going, to move as fast as she could. 

She slowed down when she finally reached her block. Her ankles were screaming from running in flimsy flats, her air was a total mess and she was breathless.

That was when she saw him. Shoulder slumped, one leg up, leaning. She knew that stance from a million miles away. 

He lifted his eyes from whatever paperback book he had been reading and his eyes brightened at the sight of her face.

“Rory,” he called out.

She broke out into a full run now, her feet slapping against the pavement as she closed the distance between them.

“Jess,” she yelled back. It was him. In his jean jacket, a backpack slung over his shoulder. His black hair hanging to the side, his mouth moving into a smile. She picked up her speed, faster than she thought she could run. And he started moving towards her too, a wild look of anticipation coming over his face. 

He dropped the bag and their bodies came together, his arms enveloping her. He held her close, squeezing her tight. 

“Jess,” she whispered, burying her face in his neck. “What the hell are you doing here?” 

“I couldn’t do it,” he whispered into her hair, pulling her even closer. “I couldn’t just...be gone.”

“I didn’t _want_ you gone.”

He pulled away from her and held her face in his hands, “I’m not going, Rory.”

“Please, don’t,” she whispered.

“Things _will_ be different.”

“They have to be.”

Placing a finger under her chin, he brought her face to his and under the streetlamp, their lips met.

In the middle of that Brooklyn street they lost themselves in each other’s arms. No more words were needed. There was no discussion. Barely taking their lips off each other, Jess picked up his bag and they made their way inside.

“Please tell me you don’t live in a fifth floor walk-up,” he murmured, pressing her against the wall of the stairwell, kissing her neck as his hands wandered to the narrowest part of her waist, making her stomach flip. She closed her eyes, suppressing a small moan of anticipation, her hands lost in his hair, “Seventh floor, actually.”

“What?!” he yanked away from her.

Rory let out a laugh. “No way. I live on the third floor.”

He rolled his eyes, “Well, I waited ten years, what’s six flights of steps?”

She feigned offense, “Whoa, there. Don’t make me change my mind.” He squeezed her waist, pressing his lips to hers again. 

She pulled away, “Message received.” 

Rory was beyond grateful she’d slugged back those two gin and tonics while she had the chance. Without them, the anticipation and anxiety of finally finding herself naked with Jess Mariano may have caused her brain to short circuit. And it was pleasantly odd for Jess to be so uninhibited, so openly affectionate and unguarded with his desire. It all still had his edge––the sarcasm, the smirk, the rolling eyes. But maybe it was experience or just time, he took the lead without question. He barely kept his hands from wandering over her collarbone, down towards her breasts, pausing only to ask, “Can I...?”

It was only when his hands found their way to the seam of her jeans and their panting became more than audible that Rory finally said, "We need to _actually_ go into my place... _now_."

Grabbing her hand and lacing her fingers with his, Jess pulled Rory up the steps, taking his mouth and hands off of her long enough only for her to unlock the door. Then he was behind her again, kissing her neck as she pulled off her coat and dropped her bag.

“Cute place,” he whispered with his usual wry tone.

She chuckled, “What’s your favorite part, the organization of my bookshelf or that lamp waaaaay over there?”

“ _Definitely_ the lamp,” and with that they fell together onto her couch, Jess's mouth moving over her jaw and neck as his hands worked to unbutton her jeans. She pushed her hands under his shirt, pulling away from him only so she could yank the shirt over his head. His chest was broad and muscular, familiar but not. He paused, sitting back on his thighs between her legs. His belt was undone, his hair ruffled.

"What?" she laughed. 

He shrugged, grinning playfully, "Who woulda thought?" 

She grabbed his belt loops and pulled him to back to her, "Shut up."

Their mouths came back together––hungry, desperate––their bodies moving in sync. No more words were needed. 

~*~

It was 3 am. They laid beside each other in her bed, clothing thrown all over her desk and chair and on the floor. A slice of moonlight filtered in through her shades and fell across his face and chest. It was funny, even in his sleep Jess looked kind of worried. She’d never really asked him about his childhood but she seeing him sleeping so peacefully, she could almost imagine it––Liz more interested in her boyfriends than his homework, his dad off with a new family. Little Jess alone with his books and his pranks. She felt a surge of affection for him and leaned over to kiss his cheek. 

His eyebrows did a little dance and he slowly blinked awake, looking at her through half-open eyes. “Rory.”

“Sorry,” she whispered. “You looked very cute and I couldn’t help myself.”

He smiled, rolling over and propping himself up on his arm. “Gee, whispering sweet-nothings to me now, are you? I'm happy I haven't scared you off.”

“Why would you have scared me?”

“Oh, I’m not sure. I’ve just been playing it so cool lately,” he smirked. 

Rory rolled her eyes, “I think it’s safe to say that the fundamental issue with our relationship was the lack of uncoolness from certain parties.”

Jess clicked his tongue, tucking a strand of hair behind her ear. “Damn, Gilmore. Take it easy on me. I’m being vulnerable here.”

“Vulnerability? Therapy? What is this, SuperSoul Sunday?”

“I told you," he said, meeting her gaze. "I want this to be different.”

She bit her lip, smiling. “Ok, but not so different that you won’t make fun of David Foster Wallace with me, right?”

“Ahh, good ol’ DFW. Have you read The Pale King yet?”

She snorted, “Boy, _have I_.” 

  
  
  


**Notes for the Chapter:**

> Long chapter this week... hope you enjoy ;)


	5. Everyone's Got a Point of View

**Summary for the Chapter:**

> He left the cabin exactly as it was, bringing only a change of clothes and his laptop, shoved quickly into his backpack. This was insane, totally off the rails. An all-around nerve-wracking, possibly horrible decision. But he had to. If he didn’t, he would regret it forever. 
> 
> Jess's point of view before meeting up with Rory.

Watching Rory drive away, Jess felt the seams of himself pulling apart. The calculated logic that drove him to return to Stars Hollow; the exceedingly level-headed decision to not get angry or upset with Nia but rather to walk away; the tightly-bond calm that had transformed “I’m so fucking in love with you” into “I still have feelings for you.” All of the broken pieces of himself Jess had stitched together into a patchwork of patience and normalcy-- of goodness he had so long thought he did not possess––threatened to come undone. He wanted a cigarette. He wanted to kick a door. He wanted to immediately run after her, throw himself in front of the car and scream, “Fuck whatever’s in New York, come with me”

But he knew how that would go.  
And he knew there was no quicker way to lose his last chance to be with Rory Gilmore. 

Jess let out a shaky breath that echoed around him in plumes of white chilled air as he stood there, unable to rip his eyes away from the flickers of her tail lights disappearing into the night. He shoved his hands into his pockets and did the only thing he could do––head home. 

He turned back towards Kelly Point Cafe and began pushing through the weeds, walking off into the marshy forest that surrounded it. Through the cold, moist air he made his way back to Taylor Doose’s cabin, his thoughts swirling in a million directions and a physical ache settling in his chest.

He didn’t think it would hurt this bad.

Before actually seeing Rory, he’d been embarrassed by these lingering feelings that seemed to dog him everywhere he turned in life. He hated the moments in the early morning when, still bleary with sleep, he’d been shocked to find Nia in bed with him and not Rory. He could barely handle the anticipation before big events at the Truncheon when he secretly hoped she’d come through those doors again. And forget about The Fountainhead; just seeing that book on the Truncheon's bookshelves did something to his soul

On the drive up from Philadelphia he’d daydreamed of locking himself away wherever-the-hell he could get a room and throwing himself fully into his writing––finishing his second novel, wrapping up his short stories for publication. But now, seeing her and sitting with her and being reminded of all of her idiosyncrasies that drove him crazy, Jess was acutely aware that these feelings didn’t want closure––they wanted to center stage. 

He wanted _her_. 

The weeds became more sparse and began to clear, opening up to a small man-made lake surrounded by pussy willow and silvergrass. Across the murk green water was a small, leaning wooden structure with an enormous wrap-around porch and warm, twinkling lights strung up around the front porch rafters. Sure, the windows were drafty and the floor squeaked constantly, but it was exactly what Jess needed. 

He made his way up the porch, tapping his phone to life. No missed calls. Only one text, from Matt. 

_Dude talked to Chris. This is fucked._

_Such comforting words,_ he thought, rolling his eyes. He wasn’t in the mood to take care of Matt, to reassure him that the business would be fine. For all they knew, he was up in Connecticut damn-near suicidal because the love of his life had cheated on him with his best friend. What he really wanted to tell Matt was that it didn’t matter. Instead, he closed out the conversation and shoved his phone back into his pocket.

Inside the cabin he threw his keys and jacket on the small wooden table that doubled as his desk and flopped down on the bed that doubled as his couch. The cabin was small but welcoming and the air permanently smelled like campfire, a scent he’d grown to love over the last week he’d spent hiding away. He picked up his worn copy of Just Kids off the nightstand and paged through to where he’d left off. It was a recent favorite of his––a book so well-written it actually made him jealous. And, try as he might, he could not seem to lose himself in Patti and Robert's world, in New York City in the 1970s. After his fifth attempt to read the same sentence, he tossed the book aside and checked his watch. Six-thirty. 

It was going to be a long night. 

He thought back to Rory’s Hemingway comment and smiled. 

_That was a compliment, right?_

_What was she going to say when she started to say, “I wish I didn’t have to…”_

_Why did I cut her off?_

_What would have happened if I…_

Jess stood up and physically shook his head, running a hand through his hair. _No._

No more thinking about Rory. This is the way things had to go. There was no other way for this to end. He never expected her to drop everything and be with him. Hell, he didn’t even expect her to agree to hanging out again. Things never seemed to really line up with them. They were always two ships, passing each other but not without scraping sides first. Leaving each other, in some way, marked for life. 

He checked his watch again. Six-thirty-three. _Damn._

A chorus of grasshoppers and cicadas drifted in through the window. His skin felt itchy and his legs restless, the weight of an entirely empty night pressing down on him. Impulsively, he pulled his phone out of his pocket and called Luke. 

~*~

God, it was weird to walk through Stars Hollow. All the storefronts and houses had stayed exactly the same for the most part, barring a few new coats of paint and some modern additions. A new crop of teenage girls had taken over the gazebo steps (they all stopped their chatting and turned their eyes on him as he walked by, causing him to double his walking speed). He’d hoped he’d picked a time early enough to miss the most invasive stares. The last time he’d made his way into town he’d found himself basically forming a blood bond with Babette, swearing her to secrecy in exchange for his first born. 

Luckily the older, and more nosy, citizens of Stars Hollow seemed to still be sleeping. 

The bell dinged as Jess opened and closed the diner’s front door. Luke looked up from behind the counter where he was starting the coffee pot, a grin breaking out over his face.

“Aren’t you a sight for sore eyes?”

Jess smirked, “I could say the same about you.”

“I’m surprised you’re here, but I’m pretty sure I don’t hate it...yet.”

Jess swung a leg over a stool and took a seat at the counter, dropping his bag on the floor. “I promise I’m way too old to be causing trouble.”

Luke scoffed and slid a mug full of dangerously hot coffee his way. “Believe me, I know. I can see some grey in that mustache. I think you may be the most successful Stars Hollow drop out.”

“Watch it. If I’m old, then what the hell are you? And don’t let them hear you say that. Pretty sure there’s still an outstanding warrant for me over some baseballs.”

Luke raised his mug to cheers. “Gotta say––looking back, that was kinda genius.”

“That’s what I tried telling you.”

Luke suddenly realized they’d been staring into each other’s eyes with intense, silent approval. He cleared his throat and they both took enormous gulps of coffee.

“So, how’s life? The lady? You two still together?” Luke asked 

Jess flicked his eyes away. “Yeah, that’s kind of why I’m here.”

Luke’s eyes widened slowly. “You’re not…”

“What?”

“You’re not having a kid, are you?”

“What?!”

“I mean you’re responsible and all––believe me, I’m really proud of you––but Jess, I’m not sure––”

“How did you get from ‘that’s kind of why I’m here’ all the way to ‘I’m having a baby’?”

Luke shook his head. “Sorry, got ahead of myself.”

“I’ll say. Nia and I are actually--uh,” Jess cleared his throat. “We’re no longer together.”

Luke’s face dropped. “Ah, Jess. I’m really sorry. I know how much you two…” he let the sentence trail off. 

Nodding, he replied, “Thanks. It’s okay. Given me a lot of time to think.”

Luke refilled Jess’s mug, an oddly warm gesture that reminded Jess why he had in a kind of, sort of way liked––maybe even sometimes loved––being around his uncle. 

“Do I dare ask about what?”

Despite his best fight, Jess could feel his cheeks starting to burn with the self-awareness of how outrageous this next statement might seem. “I’m not going to lie to you––I’ve been thinking a lot about Rory.”

Luke’s eyebrows shot up so far they almost met the edge of his baseball cap. “Rory?”

“Yes, Rory.”

“Rory Gilmore?”

“Is there another Rory in my life I should be aware of?”

“It’s been like--”

“Ten years. Yes, I know. Believe me, I am not proud of the fact that I am still––”

“In love?”

“ _Hung up_ on this girl,” Jess corrected him, cocking an eyebrow as if to say _w_ _atch it, old man._

Luke stood there, staring at his nephew, empty coffee pot hanging in his hand. Enough years had passed that Jess no longer felt the impulse to preemptively duck. With his eyes just slightly bulging out of his head, Luke kept a firm grip on the coffee pot at his side. 

“Please don’t do anything stupid, Jess. This time around I have a vested interest in you not doing something stupid.”

Jess clicked his tongue, swirling coffee around in his mug, dropping his eyes. “As much as I wish I could still access the part of my brain that was once overloaded with stupid, it seems like I am doomed to handle this responsibly. I told her how I felt and let her walk away.”

Luke kept staring. Just staring. 

“It’s over,” Jess clarified. 

“It’s _over_?” Luke shoved the coffee pot back on its stand and put his hands on his hips, a stance that still made Jess’s blood run cold. “You mean you came all the way up here, drove for hours no doubt in some shitty, used car––”

“ _Thanks._ ”

“––just so you could let her walk away?”

Jess’s eyes widened. “Are you kidding me?” he sputtered. “I’m surprised you don’t have the marching band shining their tubas out front, ready to start the celebration.”

“This really doesn’t seem like the type of thing to be joking about.”

His mouth fell open. _Was this seriously happening?_ “What do you want me to do, Luke? Chase her down?”

“W-well… yeah!”

“Are you out of your damned mind? In what universe do I have any ground to stand on in the case of ‘Please Be With Me, Rory’ colon ‘Remember When I Ran Off?’”

Luke began to pace, running a hand over his face. Jess watched the man work through his emotions. Finally, Luke stopped dead in front of him. He had his ‘I have a plan’ face on. 

“Ok, story time.”

“Dear _Lord_.”

“Nope, shut up. I’m your uncle and this is story time,” Luke said as he leaned forward onto the counter. “Once upon a time there was a very nice woman who used to come into my diner every single day with her very nice, very smart daughter. They spent nearly every night eating dinner here. Dinner made by me. They did homework here, they played games here, they made memories here. And I stood behind the counter and I watched. And I waited. Can you guess for how long?”

Jess chewed his lip for a moment. Finally, he said, “Ten years?”

Luke raised a finger, smirking. “Almost. Eight and a half. And I still managed to fuck it up a few times. But the whole time I knew, even in the worst moments, I could never let her get too far away. Sure, there were times in our lives that weren’t meant to be spent together. But there was never really anyone else. And so I never fully let her go.”

“Crazy that you feel so strongly about Miss Patty.”

Luke rolled his eyes. ‘Ok, wise guy.”

“I’m kidding, I’m kidding. And I hear you. I just can’t––”

“What, Jess? You can’t what?”

“I can’t keep showing up here every few years, looking for love from someone who...” he shook his head. He couldn’t bring himself to finish that sentence; the possibility of Rory feeling nothing for him was too painful. 

Luke stepped back to watch his nephew, crossing his arms over his chest. 

Jess exhaled slowly, steadying his breath. This was the part he had so dreaded telling Luke. “Nia cheated on me. She broke my heart. That’s what I needed to see how bad I had hurt Rory. To really see it. And sure, yes, I told her I still have feelings for her. But I think it’s best if I just move on.” After all the years of hurt and mistakes, all the fights they'd been through over this very topic, Jess had finally arrived at a conclusion he hoped would, at the very least, make Luke think that a fraction of all the mess had been worth it. 

Luke shook his head. “No.”

" _No?!_ " Jess balked, his mouth dropping and a laugh rolling out of him. "Are you kidding me?”

Luke shook his head a few more times before pulling his notepad out of his back pocket. He started frantically writing something down before ripping the paper off and handing it to Jess. 

“That’s her address in New York. She’ll be there in a few days. Go there and meet her. Don’t just tell her how you feel, _show her_. And please,” Luke leaned forward, placing his hands on both of Jess’s shoulders. “Never, ever tell Lorelai who gave you that address.”

~*~

He left the cabin exactly as it was, bringing only a change of clothes and his laptop, shoved quickly into his backpack. This was insane, totally off the rails. An all-around nerve-wracking, possibly horrible decision. But he had to. If he didn’t, he would regret it forever. 

_Life_ , he thought, _is_ _about choices_. And he had made his a long time ago.

  
  


**Notes for the Chapter:**

> Switching POV to challenge myself! Don't worry, next chapter we'll be back to Rory.


End file.
